Beta-Lapachone
Beta-Lapachone structure
|
Common Name | Beta-Lapachone | ||
|---|---|---|---|---|
| CAS Number | 4707-32-8 | Molecular Weight | 242.270 | |
| Density | 1.3±0.1 g/cm3 | Boiling Point | 381.4±42.0 °C at 760 mmHg | |
| Molecular Formula | C15H14O3 | Melting Point | >110ºC (dec.) | |
| MSDS | USA | Flash Point | 169.7±27.9 °C | |
Use of Beta-Lapachoneβ-Lapachone is a naturally occurring O-naphthoquinone, acts as a topoisomerase I inhibitor, and induces apoptosis by inhibiting cell cycle progression. |
This table lists Chinese names, IUPAC names and various aliases of this chemical substance.
| Name | β-lapachone |
|---|---|
| Synonym | More Synonyms |
This table contains bioactivity, target information and biological‑assay experimental data of this compound.
| Description | β-Lapachone is a naturally occurring O-naphthoquinone, acts as a topoisomerase I inhibitor, and induces apoptosis by inhibiting cell cycle progression. |
|---|---|
| Related Catalog | |
| Target |
Topoisomerase I |
| In Vitro | β-Lapachone is a topoisomerase I inhibitor. β-Lapachone (25 μM) inhibits camptothecin-induced DNA cleavage[1]. β-Lapachone (10-40 μM) significantly reduces the colony-forming ability of CHO cells, and is cytotoxic in S phase. β-Lapachone at above 10 μM, causes a heavy DNA-strand breaks in CHO cells[2]. β-Lapachone (10 μM) suppresses JCPyV replication in IMR-32 cells. β-Lapachone (1.0 µM) potently affects JCPyV propagation in JCI cells. β-Lapachone (0.01-0.1 μM) inhibits VP1 production in JCI cells[4]. |
| In Vivo | β-Lapachone (0.066%) ameliorates cisplatin-induced renal injury and when in combination with cisplatin, the affect is more significant in mice. β-Lapachone increases Mre11-Rad50-Nbs1 (MRN) complex expression in mice[3]. |
| Kinase Assay | DNA topoisomerase I is incubated in the presence or absence of drugs (including β-Lapachone), in 20 μL of relaxation buffer (50 mM Tris (pH 7.5). 50 mM KCl, 10 mM MgCl2, 0.5 mM dithiothreitol, 0.5 mM EDTA, 30 μg/mL bovine serum albumin) for 30 min at 37°C. Reactions are stopped by adding 1% SDS and proteinase K (50 μg/mL). After an additional 1-h incubation at 37°C, the products are separated by electrophoresis in 1% agarose gel in TAE buffer (0.04 M tris acetate, 0.001 M EDTA). The gel is stained with ethidium bromide after electrophoresis. The photographic negative is scanned with an NIH image analysis system[1]. |
| Cell Assay | Cytotoxicity is measured by an MTT assay. IMR-32 and JCI cells are plated in 96-well microtiter plates at a concentration of 5.0 × 104 (topotecan) or 2.5 × 104 (β-lapachone) cells/well/100 µL medium 24 hr prior to addition of various concentrations of topotecan or β-lapachone. The cells are then incubated for 72 hr at 37°C in a CO2 incubator. Cell proliferation is assessed using a Cell Proliferation Kit I. Experiments are performed using four independent cultures[4]. |
| Animal Admin | Male Balb/c mice are provided a commercial pellet diet and water ad libitum. After 1 week of acclimation, the mice are randomly allocated to one of the following groups (5 per group): control, β-lapachone, cisplatin (18 mg/kg, ip), and β-lapachone + cisplatin (18 mg/kg, ip). The β-lapachone groups are fed a diet containing the drug (0.066) for 2 weeks prior to cisplatin injection. All mice are sacrificed under carbon dioxide anesthesia 3 days after cisplatin injection. The blood samples are subjected to serum BUN and CRE analyses. Half of the kidney is quickly removed for histopathological and immunohistochemical (IHC) studies. The other half is stored at −70°C until western blot assay[3]. |
| References |
This table shows physicochemical parameters including melting point, boiling point, density, solubility and optical rotation. Missing data is marked as N/A.
| Density | 1.3±0.1 g/cm3 |
|---|---|
| Boiling Point | 381.4±42.0 °C at 760 mmHg |
| Melting Point | >110ºC (dec.) |
| Molecular Formula | C15H14O3 |
| Molecular Weight | 242.270 |
| Flash Point | 169.7±27.9 °C |
| Exact Mass | 242.094299 |
| PSA | 43.37000 |
| LogP | 2.82 |
| Vapour Pressure | 0.0±0.9 mmHg at 25°C |
| Index of Refraction | 1.595 |
| Storage condition | -20?C Freezer |
This table provides MSDS information including hazard classification, first‑aid, fire‑fighting, spill handling, operation and storage instructions.
This table summarizes toxicological test data, acute & chronic toxicity and ecological hazard parameters for this chemical.
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATAACUTE TOXICITY DATAMUTATION DATA
|
This table covers safety warnings, protective measures, incompatible substances and disposal guidelines for this compound.
| Personal Protective Equipment | Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter |
|---|---|
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| RTECS | QL6127400 |
| HS Code | 2914399090 |
This table presents publicly reported synthetic routes, reaction conditions, reactants and product information of the compound.
This table lists upstream starting materials and downstream derivative products related to this chemical.
| Precursor 9 | |
|---|---|
| DownStream 9 | |
CAS#:84-79-7![Naphth[2,3-b]oxirene-2,7-dione, 1a,7a-dihydro-1a-(3-methyl-2-buten-1-yl) Structure](https://image.chemsrc.com/caspic/083/137492-06-9.png)
CAS#:137492-06-9
CAS#:20213-26-7
CAS#:50-00-0
CAS#:83-72-7
CAS#:115-11-7
CAS#:107-86-8
CAS#:84-85-5![6-METHOXY-2,2-DIMETHYL-2H-BENZO[H]CHROMENE Structure](https://image.chemsrc.com/caspic/308/573-13-7.png)
CAS#:573-13-7
CAS#:111479-51-7
CAS#:27550-59-0
CAS#:53266-48-1
CAS#:88-99-3
CAS#:15298-01-8
CAS#:15297-93-5![2,2-Dimethyl-3,4-dihydro-2H-benzo[h]chromene structure](https://image.chemsrc.com/caspic/480/16274-33-2.png)
CAS#:16274-33-2![5,6-dihydro-7,7-dimethyl-7H-pyrano[3',2':4]naphtha[1,2-b]pyrazine structure](https://image.chemsrc.com/caspic/040/833122-18-2.png)
CAS#:833122-18-2
CAS#:4707-33-9This table shows customs‑related data including HS‑code, tariff and regulatory conditions for import and export.
| HS Code | 2914399090 |
|---|---|
| Summary | 2914399090. other aromatic ketones without other oxygen function. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:5.5%. General tariff:30.0% |
This table lists relevant public references with title, journal and publication metadata for this compound.
|
Light effect on the stability of β-lapachone in solution: pathways and kinetics of degradation.
J. Pharm. Pharmacol. 63(9) , 1156-60, (2011) The purpose of this work was to study the chemical stability of the new antitumoral β-lapachone (βLAP) to determine the degradation pathway/s of the molecule and the degradation kinetics in addition t... |
|
|
Temperature-sensitive gels for intratumoral delivery of β-lapachone: effect of cyclodextrins and ethanol.
ScientificWorldJournal 2012 , 126723, (2012) This work evaluated the potential of Pluronics (varieties F127 and P123) in combination with solubilizing agents to be used as syringeable in situ gelling depots of intratumoral β-lapachone (βLAP). Pl... |
|
|
Ultrastructural analysis of β-lapachone-induced surface membrane damage in male adult Schistosoma mansoni BH strain worms.
Exp. Parasitol. 142 , 83-90, (2014) The present study provides, for the first time, conclusions on the in vitro schistosomicidal properties of β-lap. Adult male Schistosoma mansoni worms of the BH strain were used for the study. Motilit... |
This table contains target information, in‑vitro & in‑vivo assay data for this compound.
This table collects all English aliases, systematic names and CAS‑related synonyms of the compound.
| 3,4-Dihydro-2,2-dimethyl-2H-naphtho(1,2-b)pyran-5,6-dione |
| Beta-Lapachone |
| 3,4-Dihydro-2,2-dimethyl-2H-naphtho[2,3-b]pyran-5,10-dione |
| β-lapachone |
| 3,4-dihydro-2,2-dimethyl-2H-naphthol[1,2-b]-pyran-5,6-dione |
| 2,2-Dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione |
| 2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione |
| ARQ-501 |
| CO-501 |
This section contains frequently‑asked‑questions about this compound, including basic parameters, properties, storage conditions and corresponding answers.
| Q: What is the polar surface area (PSA) of β-lapachone? |
| A: Polar surface area (PSA) of β-lapachone is 43.37000. |
| Q: What are the downstream products of β-lapachone? |
| A: Related downstream products(CAS) of β-lapachone: 111479-51-7;27550-59-0;53266-48-1;88-99-3;15298-01-8;15297-93-5;16274-33-2;833122-18-2;4707-33-9. |
| Q: What is the molecular weight of β-lapachone? |
| A: Molecular weight of β-lapachone is 242.270. |
| Q: What is the English name of β-lapachone? |
| A: The English name of β-lapachone is β-lapachone. |
| Q: What are the upstream materials of β-lapachone? |
| A: Related upstream materials(CAS) of β-lapachone: 84-79-7;137492-06-9;20213-26-7;50-00-0;83-72-7;115-11-7;107-86-8;84-85-5;573-13-7. |
| Q: What are the uses of β-lapachone? |
| A: Main uses of β-lapachone: β-Lapachone is a naturally occurring O-naphthoquinone, acts as a topoisomerase I inhibitor, and induces apoptosis by inhibiting cell cycle progression. |
| Q: What are the storage conditions for β-lapachone? |
| A: Storage conditions for β-lapachone: -20?C Freezer. |
| Q: What English synonyms does β-lapachone have? |
| A: English synonyms of β-lapachone: 3,4-Dihydro-2,2-dimethyl-2H-naphtho(1,2-b)pyran-5,6-dione, Beta-Lapachone, 3,4-Dihydro-2,2-dimethyl-2H-naphtho[2,3-b]pyran-5,10-dione, β-lapachone, 3,4-dihydro-2,2-dimethyl-2H-naphthol[1,2-b]-pyran-5,6-dione, 2,2-Dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione, 2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione, ARQ-501, CO-501. |
| Q: What is the molecular formula of β-lapachone? |
| A: Molecular formula of β-lapachone is C15H14O3. |
| Q: What is the melting point of β-lapachone? |
| A: Melting point of β-lapachone is >110ºC (dec.). |
This table lists manufacturers and suppliers of this compound, including vendor names and product supply reference information.
| Shanghai Nianxing Industrial Co., Ltd |
| Dayang Chem (Hangzhou) Co., Ltd. |